I know that shift + select should result in multiple selections, but it doesn’t work in Libre Office Writer. When I try to select a second object, the original selection I made is transferred to the object nearest the top of the page. This happened also when I had Libre loaded on my other laptop.
That’s probably → Bug 37960 - Shift click to select multiple drawings does not work if picture there.
It is not possible either using the selection cursor from drawing tool bar → Bug 40854 - EDITING - impossible to select multiple drawing objects when a image is inserted.
For the record: fdo#40854 has been marked as a duplicate of fdo#37960.
Current status of fdo#37960 is NEW
Resolving as BUG FILED